That's a hard thing to predict. There are two key factors in the Chicago market that will be affecting pricing. First, the area unemployment is above 10%. That has a huge affect on the area as those who are unemployed cannot purchase homes. Its not a coincidence that the national mortgage delinquency rate is also above 10%. If this number does not come down, you will probably not see home prices improving.
Second, property taxes were reassessed this year and some areas have gone up. I read in the Tribune that some areas of Garfield Park went up 40%. The rise in property taxes will have a negative affect on property pricing.